Modular Synthesis of the Nonadecasaccharide Motif of Psidium guajava Polysaccharides: Orthogonal One-Pot Glycosylation Strategy
Modular Synthesis of the Nonadecasaccharide Motif of Psidium guajava Polysaccharides: Orthogonal One-Pot Glycosylation Strategy
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番石榴多糖十九糖基序的模块化合成：正交一锅法糖基化策略
DOI：
10.1002/anie.202000992
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Guozhi Xiao
中科院分区：
文献类型：
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作者：
Yunqin Zhang;Zixi Chen;Yingying Huang;Shaojun He;Xingkuan Yang;Zhibing Wu;Xiufang Wang;Guozhi Xiao
长的、分支的和复杂的碳水化合物序列的合成仍然是化学合成中具有挑战性的任务。本文报道了一种高效且模块化的一锅法合成九碳糖和来自番石榴多糖的较短序列，这些糖具有强效的α-葡萄糖苷酶抑制活性。该合成策略的特点是：1）基于N-苯基三氟乙酰亚胺酯（PTFAI）和Yu糖基化的几个一锅糖基化反应，以简化寡糖的化学合成，2）成功和有效的组装序列（第一个O3′，第二个O 5 ′，最后一个O2′）朝向具有挑战性的2，3，5-支化Araf基序，3）通过试剂控制的立体选择性1，2-顺式-葡萄糖基化，以及4）收敛的[6+6+7]一锅偶联反应，用于最终组装目标十九糖。 这种正交一锅糖基化策略可以简化长的、分支的和复杂的碳水化合物链的化学合成。
The synthesis of long, branched, and complex carbohydrate sequences remains a challenging task in chemical synthesis. Reported here is an efficient and modular one‐pot synthesis of a nona‐decasaccharide and shorter sequences fromPsidium guajavapolysaccharides, which have the potent α‐glucosidase inhibitory activity. The synthetic strategy features: 1) several one‐pot glycosylation reactions on the basis ofN‐phenyltrifluoroacetimidate (PTFAI) and Yu glycosylation to streamline the chemical synthesis of oligosaccharides, 2) the successful and efficient assembly sequences (first O3′, second O5′, final O2′) toward the challenging 2,3,5‐branched Arafmotif, 3) the stereoselective 1,2‐cis‐glucosylation by reagent control, and 4) the convergent [6+6+7] one‐pot coupling reaction for the final assembly of the target nona‐decasaccharide. This orthogonal one‐pot glycosylation strategy can streamline the chemical synthesis of long, branched, and complicated carbohydrate chains.